Hydrochloric Acid → 6-Hydroxy-1,3-benzothiazole-2-carboxylic acid

HRID 539821Notes

Reaction equation

HRID 539821 reaction equation
[OH:1][C:2]1[CH:14]=[CH:13][C:5]2[N:6]=[C:7]([C:9]([O:11]C)=[O:10])[S:8][C:4]=2[CH:3]=1.[OH-].[Na+].Cl>>[OH:1][C:2]1[CH:14]=[CH:13][C:5]2[N:6]=[C:7]([C:9]([OH:11])=[O:10])[S:8][C:4]=2[CH:3]=1

Participants

4

Reactant 3

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 15106734Methyl 6-hydroxybenzothiazole-2-carboxylate

Product 1

HCID 154983676-Hydroxy-1,3-benzothiazole-2-carboxylic acidYield 102.5%

Procedure

A mixture of methyl 6-hydroxybenzo[d]thiazole-2-carboxylate (0.21 g, 1 mmol) and 1N aqueous sodium hydroxide (2 mL) was stirred at room temperature overnight. The reaction mixture was then carefully acidified with concentrated hydrochloric acid. The precipitate formed was filtered, washed with water, and dried under reduced pressure to afford 6-hydroxybenzo[d]thiazole-2-carboxylic acid as a white solid (0.20 g, 99%). 1H-NMR (DMSO-d6, 300 MHz): δ 10.20 (s, 1H), 7.96 (m, 1H), 7.44 (m, 1H), 7.06 (m, 1H) ppm; MS (ESI): 196.1 (M+1).

Workup

  1. customThe precipitate formed
  2. filtrationwas filtered
  3. washwashed with water
  4. customdried under reduced pressure

Sources & evidence

ORD record
ord-d5b6a5469e724c28ae0e2190cf73f06f
Source dataset
uspto-grants-2014_10
Patent number
US08871770B2

Reaction notes

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